Hydrochloric Acid → 5-Bromo-4-(3-chloro-4-fluorophenyl)-1,3-thiazole-2-carboxylic acid

HRID 2038364Notes

Reaction equation

HRID 2038364 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]([O:9]CC)=[O:8])=[N:4][C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([F:18])=[C:14]([Cl:19])[CH:13]=1.[OH-].[Li+].O.Cl>O1CCCC1>[Br:1][C:2]1[S:6][C:5]([C:7]([OH:9])=[O:8])=[N:4][C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([F:18])=[C:14]([Cl:19])[CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 70801639Ethyl 5-bromo-4-(3-chloro-4-fluorophenyl)-1,3-thiazole-2-carboxylate

Product 1

HCID 708016435-Bromo-4-(3-chloro-4-fluorophenyl)-1,3-thiazole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

400 mg (1.10 mmol) of the compound from Example 4A are provided in 19 ml of tetrahydrofuran, and 263 mg (11.0 mmol) of lithium hydroxide and 19 ml of water are added at room temperature. The mixture is stirred at room temperature overnight, a 1N aqueous hydrogen chloride solution is then added until an acidic pH is achieved, the mixture is extracted with ethyl acetate and the organic phase is washed with water, dried over sodium sulfate, filtered and concentrated. 190 mg of the title compound having a purity of 86% (44% of theory) are obtained.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washthe organic phase is washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customare obtained

Sources & evidence

ORD record
ord-2b0ebf1fc82d49ff8875df76ba6ab2b1
Source dataset
uspto-grants-2013_11
Patent number
US08575357B2

Reaction notes

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